


the ending we deserve

by Anonymous



Category: Critical Role (Web Series)
Genre: (idk who made that rule up but I'm not about to break it), (tiefling dicks have ridges), Future Fic, Hair Pulling, Light Spanking, M/M, Oral and Anal Sex, PWP, cis!Caleb, dom!Essek, ftm Essek, inappropriate timing of a sending spell, incredibly bisexual Caleb Widogast, sex with feelings, some tender boys here, submissive!caleb, this isn't a d/s fic but Essek has some naughty thoughts in that direction, tiefling dick dildo, trans!Essek
Language: English
Status: Completed
Published: 2020-03-31
Updated: 2020-03-31
Packaged: 2021-03-01 01:22:03
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,531
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23406685
Author URL: https://archiveofourown.org/
Summary: Essek and Caleb, a few years into the future, deeply in love with one another still.[PWP, tenderness, trans!Essek and cis!Caleb]
Relationships: Essek Thelyss/Caleb Widogast
Comments: 4
Kudos: 197
Collections: Anonymous





	the ending we deserve

**Author's Note:**

> I am a cis person so hopefully I got the trans stuff right. If I did not let me know and I will fix it immediately.

“You’re so _wet_ ,” Caleb marvels, wandering fingers having found their way into Essek’s pants, into his undergarments, fondling him, gentle fingers running along his cock, against his folds. “And so _hard._ Already?”

_Of course I am_ , Essek thinks, face flushed slightly as his lover’s long fingers caress his thighs. _You spent the last_ **_hour_ ** _of the party_ **_teasing_ ** _me._

He doesn’t say that; instead, he grabs Caleb’s ascot and drags him into a kiss. “Are you going to do something about that?” He asks when they pull apart to breathe. 

Caleb’s wide grin is answer enough.

After that, it’s a race to undress and a race to the bed. Jacket, shirt, pants, boots, heels, scarf--all discarded clumsily, making a mess of his bedroom. He keeps his binder on, though, silk and magic against his skin, as he lays down flat in the center of his bed, arms spread across the width, beckoning his lover forward. 

Caleb takes a little longer to undress, struggling not to fall over as he takes his socks off one at a time, but then he jumps on top of Essek, kissing him.

They kiss for a little bit, hands exploring flesh, tongues tasting one another, but Caleb gets impatient. He always gets impatient first. “May I suck your cock?” He asks sweetly, pressing a kiss to his neck, to his clavicle, right above his heart. 

Essek _loves_ him, has loved him for years, could never deny him anything, but especially not that, so he kisses him again. “Of course.”

Then he grabs his hair, and shoves him downward.

Caleb immediately starts kissing his thigh, sucking a bruise into dark purple skin. His nose brushes against Essek’s stark white curls, and he breathes in the scent. “And may I, here? Or would you prefer I just focus on your cock tonight?”

He loves that he asks, because there are days where the answer is no, where he cannot stand the thought of his love touching his cunt. Today, he doesn’t find that he minds much, though. “You can have both,” he tells him, running his hands through Caleb’s hair.

His cock isn’t very big; he knows, with magic, he could make it bigger, could get rid of his cunt and breasts all together, but he hasn’t, yet. Doesn’t know if he’ll ever. He kind of likes his body now, most days. People who see him on the street assume (correctly) that he’s a man, and Caleb, bless him, doesn’t seem to have a preference for body parts, and enjoys worshiping Essek’s body because it’s _Essek’s_ body, and not for any other reason. Essek could have a mass of tentacles, he thinks, and Caleb would still love him, simply because he’s _Essek_.

There were times previously when his insecurity would eat away at him. Former lovers who would make comments that would linger in his psyche like a permanent scar, but having Caleb like this is like a balm, a cure to a wound long since forgotten about.

Caleb likes his body too; he hums with pleasure as he takes his cock in his mouth, sucking gleefully on his length. The entire thing fits in his mouth easily, but he’s never seemed to mind that, just enjoys the taste and feel of him.

Above him, Essek grasps at the sheets.

Then Caleb stops, suddenly, and pulls away, leaving Essek dazed and confused, panicked at the sudden absence of Caleb. When he looks down at his lover, his eyes are closed, and he holds up a finger, as if to say _just a moment._

“ _Jester_ ,” he growls, and Essek cannot help but snort with laughter. “I’m a little busy. I went home with Essek. Yes, we had fun at the party. Sorry I didn’t tell you guys--I’ll see you.” Out of words as the spell fizzles, Caleb rolls his eyes at Essek, and blushes slightly. “Sorry about that. She has- _-terrible_ timing, sometimes.”

But Essek only snorts back at him. “I understand,” he then taps Caleb’s cheek, as if to tell him to continue.

But before Caleb can move, Essek has to grab his hair to stop him, his own mind now harassed by a similar spell. _Essek are you and Caleb having sex??? He was really weird and didn’t want to answer my questions! You_ **_are_ ** _having sex aren’t you? Veth owes--_ The spell finishes, and Essek groans, slamming his head back down against the pillow.

“Jester Lavorre,” Essek says through gritted teeth, one hand still holding Caleb’s hair firmly. “You are my dearest friend. But if you message either of us in the next,” ten? Twenty? “Thirty minutes, I will _disintegrate you myself._ ”

He swears he can hear her giggling as the spell fades, even though he knows that’s not how the spell works. 

They stay quiet for a moment, afraid of another message incoming, Caleb’s face resting gently on his thighs. “Think we’re safe?” his lover asks, kissing his thighs again, this time trying to add a matching bruise to the other side.

“I think so,” Essek says softly, gently running his fingers through Caleb’s hair.

Caleb doesn’t wait for further instructions; instead, he buries his face into his curls, lapping gently at the folds there. He alternates his attention, spending a few moments sucking on his cock, then a few moments with his tongue exploring his warmth, then back to his cock. One of the things he loves about Caleb is that Caleb worships his body like his body is a pleasure for Caleb, too, like he gets just as turned on sucking on Essek’s cock as Essek does. He doesn’t get as wet as he used to, but Caleb laps at his folds greedily anyway, chasing after the taste of him.

Essek’s orgasm hits powerfully, leaving him loose and lovesick, boneless against the sheets. An hour of Caleb’s teasing at the party--hands caressed against his ass while in the crowd, fingers trailing the inside of his thighs beside him at dinner, a kiss, too long to be polite--and then having his love’s direct attention for several minutes means that he didn’t last long at all, but he finds he’s okay with that. 

When he looks back down again, Caleb’s got cum drenched in his beard, and he’s pressing gentle kisses against Essek’s belly, his nose brushing up against the silk of Essek’s binder. Softly, Essek grabs at his cheeks and pulls him upward to kiss him. The taste of himself on Caleb’s mouth isn’t the most enjoyable thing in the world, but he finds he loves him too much to care.

But Caleb’s cock is hard against his stomach, and hard to ignore, even as Caleb seems more focused on kissing him than anything else. Essek’s hand trails down and cups his length, grazing like a tease. 

Caleb groans, and breaks apart from him. “What are you doing?”

“Trying to decide how I want you,” Essek answers coyly, pressing gentle kisses against Caleb’s neck. “I have ideas. But I was wondering if you had any thoughts?”

He bites at Caleb’s neck, _hard_ and sharp, not quite drawing blood but bruising, certainly, and Caleb answers his question with a moan.

“I could suck you off,” Essek muses, one hand toying with Caleb’s hair. “I do so love having you in my mouth.”

“Mmmmph,” Caleb gasps as Essek’s other hand plays with his member. “That’s ah, a good idea.”

“Or I could let you fuck me, because that’s real nice, too,” he runs a hand through Caleb’s hair, and _tugs_ at it, pulling it sharply. “Or I could fuck you.”

“ _That_ one,” Caleb moans, eyes sparkling with glee. “Would be my preference.”

“It’s a good choice,” Essek teases him, fingers feather light against his cock. He then smacks him on the ass sharply. “Go, pick out a nice cock for me, yeah? I’ll get everything else ready.”

“Yessir,” Caleb grins, then hops from the bed to the closet, to admire Essek’s rather impressive collection. “Do you have a preference?”

He waves him off. “Whatever you want, honey,” he tells him, opening the drawer underneath his nightstand. He thinks he knows what cock the red-head will pick, but he’s been surprised before. He pulls out the strap on and starts hooking it onto his hips, tight leather against his skin. He likes wearing this for several reasons, but the tightness of the leather feels almost like being bound, and he finds he likes that feeling.

He likes it even better when he’s in control of the situation.

Giddy with excitement, Caleb comes rushing back from the closet. The large red tiefling dildo in his hands is a mild surprise, not quite what Essek was expecting, but not out of character. Caleb tends to enjoy the exotic; he enjoys things that are less human-looking in nature in general. Tiefling dicks aren’t too far from human ones, but they do have ridges, and the size of this one is--certainly not the _largest_ one in Essek’s collection, but among the bigger ones, certainly. 

“I forgot I owned this one,” Essek muses, taking the cock from Caleb’s hands to put in his strap.

“ _I_ didn’t,” Caleb practically vibrates with excitement, kneeling on the bed. He’s like a puppy, almost, finding it difficult to sit still on the bed. He’d look good with a collar on, Essek thinks. “I’ve been wanting to try it since I saw it a few weeks ago.”

“You should have said something,” Essek teases him, finding lube in the drawer, taking measures to make sure the cock is wet enough. “I would have used it last time if I’d known.”

“I’m not complaining about last time,” Caleb raises his eyebrows pointedly in Essek’s direction. “I _quite_ enjoyed myself last time.”

As did Essek, of course, but that wasn’t the point. “Hm. Bend over.”

Caleb does, of course, getting on all fours across the length of the bed. Essek coats his fingers liberally, and then begins the process of opening Caleb up. His lover moans as he fingers him, gently moving in and out, in and out. As his fingers move Essek kisses at freckles on Caleb’s back, taking his time tracing star constellations in his skin.

“You could move a little faster, you know,” Caleb grunts as Essek slowly adds a second finger, continuing his gentle stretch.

“And rush this?” He bends his fingers slightly, causing Caleb to gasp.

“ _You’ve_ already come once tonight,” Caleb complains as Essek slowly--ever so slowly--moves his fingers in and out. 

“And I’ll likely come again,” he kisses his favorite freckle on Caleb’s back, the one right beneath his shoulder blade. “And so will you. Let me _enjoy_ you, my lovely.”

He slides a third finger into Caleb, really stretching him open now, but more importantly, enjoying the little sounds of pleasure Caleb makes as he does so. 

“I’m ready,” Caleb breathes, and Essek removes his fingers entirely, smacking him lightly on the ass.

“ _I_ decide that,” he tells his love, and goes back to fingering him again, just out of spite. For all Caleb’s complaining, though, he loves this part, the preparation, and he knows Caleb loves it too.

Finally, he decides he’s teased Caleb enough. He grabs him by the hair and pulls on his ponytail. “Think you can stand for this?”

“Hmm?” Caleb groans, his head in the pillow as he lifts up from it. “Yeah, sure.”

Caleb scoots off the bed but stands against it, his knees brushed against the bedframe, and Essek wraps his arms around Caleb’s waist, pulling him closer, his ass rubbing against the cock Essek wears. “I love you,” Essek whispers, biting at his lover’s ear.

“I love you to _\--oooh_ ,” Caleb moans as Essek slides the bright red cock inside of him. He can’t feel what it feels like to be inside Caleb, but he imagines it’s tight, and warm, that it feels just as nice for Caleb like it does for Essek, when Caleb does this to him.

Standing like this, Caleb is significantly taller than him, but not so tall that Essek can’t fit inside him still. What it means is that Essek gets to keep kissing on Caleb’s back and shoulders, arms wrapped around Caleb’s waist as he thrusts into him, in and out, in and out.

“You like the ridges?” Essek asks coyly, one of his hands moving from it’s sentinel position holding Caleb’s hips to play instead with his cock, pumping him in time with his thrusts. Caleb’s breathing is whiny and unfocused, hips thrusting in time with Essek’s movements, and Essek loves it when he gets like this, so desperate to come that he’s practically shaking, vibrating in his skin. “Does it feel good?”

“ _Yes!”_ Caleb practically screams, his hips moving faster now, desperate to come. Essek loves him like this, loves making him feel so good he can’t hardly stand it anymore. “Yes, Essek, _please,_ I--”

He doesn’t get to finish his sentence; Essek thrusts into him instead, hits him in _just_ the right spot, and bites at his neck, and then Caleb comes all over Essek’s hand and his own stomach, his limbs loose and barely able to stand.

With a slight _pop_ , Essek slides the cock out of him, and pushes Caleb face-first into the bed, discarding him like a well-used toy. Caleb doesn’t seem to mind, though, drooling on the blankets, his hole a pretty pink, shiny from the lubricant. 

Essek smacks him again, lightly, just because he can, enjoying the shocked little yelp Caleb gives in response. He slides the strap on off of his waist, leaving it and the dildo on the floor before jumping on the bed beside Caleb.

Caleb is...already drooling, and his eyes are closed. He looks blissful like this, strung out and well-fucked, and Essek would memorize this moment if he could.

Instead, he takes a moment to pull Caleb closer and kiss him sweetly. “This is why you don’t get to come first,” he teases, wrapping his arms around Caleb’s back. He lays his head down on Caleb’s chest instead, rubbing his face against Caleb’s chest hair. “You are _useless_ afterwards.”

Between his legs, his arousal is apparent but not overwhelming. He _could_ come again, but it’ll go away if he ignores it. Besides, cuddling with Caleb is his favorite part of the night, almost worth not getting to come again.

“‘m not useless,” Caleb grumbles, his eyes still closed even as he wraps his arms around Essek, holding him close, legs and arms entangling him like an overly furry octopus. “I’ll eat you out again if you want.”

Essek laughs as Caleb rubs his scruffy beard face against him, peppering him with kisses. “I’d sit on your face and you’d drown,” Essek teases, squirming against him. It’s a little warm, being in both his binder and having Caleb wrapped around him like he is, but he can’t be bothered to take it off right now. “Or suffocate. Look at you, you’re half asleep already!” 

“Mmmh. What a way to go, though,” Caleb muses, and kisses him again, and then he’s asleep, and Essek’s not far behind him.

  
  



End file.
